Synthesis of a model compound of corydendramine A

CHED 477

Tiffani N. Gruber, tgruber@mail.csuchico.edu and Christopher J. Nichols, cjnichols@csuchico.edu. Department of Chemistry and Biochemistry, California State University, Chico, 400 W. First Street, Chico, CA 95929-0210
Corydendramine A (1) was isolated from Corydendrium parasiticum in 2001 and has activity as a fish-feeding deterrent. A model compound (2) has been synthesized in 8 steps overall from 2-piperidinemethanol and trans-cinnamaldehyde, using a Julia coupling in the key step. HPLC analysis of the Julia coupling showed a 3:2 ratio of E to Z alkenes formed. Reasonable to good yields were obtained in each of the other synthetic steps.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008